3-Indolylacetonitrile (CHEM008174)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:40:06 UTC
Update Date2016-11-09 01:13:44 UTC
Accession NumberCHEM008174
Identification
Common Name3-Indolylacetonitrile
ClassSmall Molecule
DescriptionA nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.
Contaminant Sources
  • FooDB Chemicals
  • My Exposome Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(indol-3-yl)AcetonitrileChEBI
(Indole-3-yl)acetonitrileChEBI
3-(Cyanomethyl)indoleChEBI
3-IndolylacetonitrileChEBI
indol-3-YlacetonitrileChEBI
Indole-3-acetonitrileKegg
(3-Indolyl)acetonitrileHMDB
1H-indol-3-YlacetonitrileHMDB
1H-Indole-3-acetonitrileHMDB
3-Cyanomethyl-1H-indoleHMDB
3-IndolacetonitrileHMDB
3-Indolyl-acetonitrileHMDB
b-IndoleacetonitrileHMDB
beta-IndoleacetonitrileHMDB
IANHMDB
IndoleacetonitrileHMDB
Indolyl-3-acetonitrileHMDB
IndolylacetonitrilHMDB
IndolylacetonitrileHMDB
Usaf CB-29HMDB
3-IndoleacetonitrileChEBI
(1H-Indol-3-yl)acetonitrileHMDB
Chemical FormulaC10H8N2
Average Molecular Mass156.184 g/mol
Monoisotopic Mass156.069 g/mol
CAS Registry Number771-51-7
IUPAC Name2-(1H-indol-3-yl)acetonitrile
Traditional Nameindole-3-acetonitrile
SMILESN#CCC1=CNC2=C1C=CC=C2
InChI IdentifierInChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
InChI KeyDMCPFOBLJMLSNX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP2.73ALOGPS
logP1.77ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.58 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.43 m³·mol⁻¹ChemAxon
Polarizability16.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-2950000000-640d53401ab5b06bad68Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-1930000000-26ddd3b2caf5e0b3a5b6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00fr-9740000000-96b8f06c6fb07ce93a3cSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-2950000000-640d53401ab5b06bad68Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0930000000-32debced08db3d4bf8cbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-0900000000-8282b286970c64cd1738Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-458b38914f7ddf5b481aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-4900000000-69f7e3dfc4f01efba464Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9300000000-7e44794a04e8de3d1dafSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-d454501befd7405d3a7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e95beea8400e01e0632aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-42b4258b99c8588269deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-dba18a56ff6cbe01fe5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-cc0c89a2abe2633a9003Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0900000000-1d1a4eca72f57a9b927cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02ai-5900000000-bac26e180028ec3a808fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-016r-7900000000-8ee8a1b5f235ed461d7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-4900000000-3e3f0478af07473aa142Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-1af02646eabe1e90e482Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-686ec8d86a82008f6a87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-0f41c00c3703e04901e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-1900000000-144022b6dfec80ddd4a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0adeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-9b52919ba61c73ce0adeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-f8b24a877c386d550c92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-fc82dffe3b09577e06eeSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-2900000000-be863c7acf7363ffeedcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006524
FooDB IDFDB001365
Phenol Explorer IDNot Available
KNApSAcK IDC00000107
BiGG ID1724337
BioCyc IDINDOLEYL-CPD
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID312357
ChEBI ID17566
PubChem Compound ID351795
Kegg Compound IDC02938
YMDB IDNot Available
ECMDB IDM2MDB004427
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11867093
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20649646
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21619597
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2342128
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24837382
6. Ahmad, A.; Spenser, Ian D. 3-Indolepyruvic acid oxime as the precursor of 3-indoleacetonitrile. Canadian Journal of Chemistry (1960), 38 1625-34.
7. Ahmad, A.; Spenser, Ian D. 3-Indolepyruvic acid oxime as the precursor of 3-indoleacetonitrile. Canadian Journal of Chemistry (1960), 38 1625-34.
8. Ciska E, Pathak DR: Glucosinolate derivatives in stored fermented cabbage. J Agric Food Chem. 2004 Dec 29;52(26):7938-43.
9. Smith TK, Lund EK, Clarke RG, Bennett RN, Johnson IT: Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. J Agric Food Chem. 2005 May 18;53(10):3895-901.
10. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9.
11. Bradlow HL, Hershcopf R, Martucci C, Fishman J: 16 alpha-hydroxylation of estradiol: a possible risk marker for breast cancer. Ann N Y Acad Sci. 1986;464:138-51.
12. Degawa M, Kojima M, Hishinuma T, Hashimoto Y: Sex-dependent induction of hepatic enzymes for mutagenic activation of a tryptophan pyrolysate component, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]-indole, by feeding in mice. Cancer Res. 1985 Jan;45(1):96-102.
13. Bradfield CA, Bjeldanes LF: Effect of dietary indole-3-carbinol on intestinal and hepatic monooxygenase, glutathione S-transferase and epoxide hydrolase activities in the rat. Food Chem Toxicol. 1984 Dec;22(12):977-82.
14. Eisele TA, Bailey GS, Nixon JE: The effect of indole-3-carbinol, an aflatoxin B1 hepatocarcinoma inhibitor, and other indole analogs on the rainbow trout hepatic mixed function oxidase system. Toxicol Lett. 1983 Oct-Nov;19(1-2):133-8.
15. Nixon JE, Hendricks JD, Pawlowski NE, Pereira CB, Sinnhuber RO, Bailey GS: Inhibition of aflatoxin B1 carcinogenesis in rainbow trout by flavone and indole compounds. Carcinogenesis. 1984 May;5(5):615-9.
16. Kappas A, Anderson KE, Conney AH, Pantuck EJ, Fishman J, Bradlow HL: Nutrition-endocrine interactions: induction of reciprocal changes in the delta 4-5 alpha-reduction of testosterone and the cytochrome P-450-dependent oxidation of estradiol by dietary macronutrients in man. Proc Natl Acad Sci U S A. 1983 Dec;80(24):7646-9.
17. Anderson KE, Kappas A, Conney AH, Bradlow HL, Fishman J: The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J Clin Endocrinol Metab. 1984 Jul;59(1):103-7.
18. Bulger WH, Kupfer D: Effect of xenobiotic estrogens and structurally related compounds on 2-hydroxylation of estradiol and on other monooxygenase activities in rat liver. Biochem Pharmacol. 1983 Mar 15;32(6):1005-10.
19. Shertzer HG: Indole-3-carbinol and indole-3-acetonitrile influence on hepatic microsomal metabolism. Toxicol Appl Pharmacol. 1982 Jun 30;64(2):353-61.
20. Barngrover DA, Stevens HC, Dills WL Jr: D-Xylulose-1-phosphate: enzymatic assay and production in isolated rat hepatocytes. Biochem Biophys Res Commun. 1981 Sep 16;102(1):75-80.
21. GHALAMBOR MA, HEATH EC: The metabolism of L-fucose. II. The enzymatic cleavage of L-fuculose 1-phosphate. J Biol Chem. 1962 Aug;237:2427-33.
22. James HM, Bais R, Edwards JB, Rofe AM, Conyers AJ: Models for the metabolic production of oxalate from xylitol in humans: a role for fructokinase and aldolase. Aust J Exp Biol Med Sci. 1982 Feb;60(Pt 1):117-22.
23. Bais R, James HM, Rofe AM, Conyers RA: The purification and properties of human liver ketohexokinase. A role for ketohexokinase and fructose-bisphosphate aldolase in the metabolic production of oxalate from xylitol. Biochem J. 1985 Aug 15;230(1):53-60.